1. Field of the Invention
This invention relates to certain novel sulfonylhydrazones of 1,4-dioxoquinoxaline-2-carboxaldehyde, 4-oxoquinoxaline-2-carboxaldehyde, certain derivatives thereof and to their use as antibacterial agents and for promoting growth and improving feed efficiency in animals.
2. Description of the Prior Art
Schiff bases derived from 2-formylquinoxaline-1,4-dioxides and carbonyl-containing hydrazine derivatives are well known compounds, some of which are useful as antibacterial agents and are valuable as growth promoting agents in animals. U.S. Pat. No. 3,371,090 discloses Schiff bases of the formula: ##STR2## wherein R.sub.1 and R.sub.2 are each hydrogen and lower alkyl; R.sub.3 is selected from the group consisting of NHCSNH.sub.2, NHC(NH)NH.sub.2, NHR.sub.4, NHCOOR.sub.5, NHCOR.sub.6, OR.sub.7, ##STR3## wherein R.sub.4 is lower alkyl, benzyl or hydroxyalkyl having from 2 to 4 carbon atoms; R.sub.5 is lower alkyl, hydroxyalkyl having from 2 to 4 carbon atoms or haloalkyl having from 2 to 4 carbon atoms; R.sub.6 is lower alkyl or phenyl; and R.sub.7 is lower alkyl. Methods for promoting growth and improving feed efficiency of animals and animal feed compositions employing these compounds are disclosed in U.S. Pat. No. 3,433,871.
Arylsulfonylhydrazones of formylpyridine N-oxides, 2-formylquinoline N-oxide phenylsulfonylhydrazone and the corresponding 1-formylisoquinoline compound were recently reported by Sartorelli et al., J. Med. Chem., 19, 830 (1976). The 2-formylpyridine-N-oxide arylsulfonylhydrazones were found to have tumor inhibiting properties. However, replacement of the pyridine ring with benzene, quinoline or isoquinoline resulted in loss of activity; movement of the formylsulfonylhydrazone side chain from the 2 to the 3 or 4 position of the pyridine-N-oxide also produced inactive compounds; and replacement of the SO.sub.2 by C.dbd.O resulted in complete loss of activity.